Hydrochloric Acid → 3-(2,6-difluorophenyl)-5-hydroxy-5-methyl-4-phenyl-2(5H)-furanone

HRID 511742

反応式

HRID 511742 の反応式
Br[CH:2](C)[C:3]([C:5]1C=CC=CC=1)=[O:4].[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[CH2:20][C:21]([OH:23])=[O:22].[CH2:24]1[CH2:34][CH2:33]N2[C:27](=NCCC2)[CH2:26][CH2:25]1.Cl>C(N(CC)CC)C.C(#N)C>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[C:20]1[C:21](=[O:23])[O:22][C:3]([OH:4])([CH3:5])[C:2]=1[C:27]1[CH:26]=[CH:25][CH:24]=[CH:34][CH:33]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 164522-BromopropiophenoneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2 回HCID 1235852,6-Difluorophenylacetic acid

生成物 1

HCID 680100533-(2,6-difluorophenyl)-5-hydroxy-5-methyl-4-phenyl-2(5H)-furanone収率 93.7%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒

実験手順

To a mixture of 2-bromopropiophenone (2.13 g), 2,6-difluorophenylacetic acid (1.81 g) and acetonitrile (25 mL), triethylamine (1.52 g) was added dropwise in a water bath, stirred at room temperature for 4 hours and then allowed to stand still overnight. To the mixture, 4.57 g of 1,8-diazabicyclo[5.4.0]-7-undecene (hereinafter, referred to as DBU) was added dropwise under ice cooling. The mixture was stirred at room temperature for one hour. Thereafter, to the obtained mixture, air was blown in while stirring at room temperature for 5 hours. To the reaction mixture, ice and 1 mol/L hydrochloric acid were added. The mixture was extracted with ethyl acetate. The organic layer was sequentially washed with a saturated aqueous sodium bicarbonate solution and a saturated saline solution, dried over an anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 3-(2,6-difluorophenyl)-5-hydroxy-5-methyl-4-phenyl-2(5H)-furanone (2.83 g).

後処理

  1. additionwas added dropwise in a water bath
  2. waitto stand still overnight
  3. additionwas added dropwise under ice cooling
  4. stirringThe mixture was stirred at room temperature for one hour
  5. stirringwhile stirring at room temperature for 5 hours
  6. extractionThe mixture was extracted with ethyl acetate
  7. washThe organic layer was sequentially washed with a saturated aqueous sodium bicarbonate solution
  8. dry with materiala saturated saline solution, dried over an anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-121a8a6bb2e34fedaeda3c0c2724657a
出典データセット
uspto-grants-2015_08
特許番号
US09101139B2

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